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An immaculately restored whaler’s house in Sag Harbor; brokers, without irony, call it a farmhouse, oh well; conventional, that’s qualified praise; when a house becomes a collector’s item

Main Street Matters

The whaling industry brought significant prosperity to Sag Harbor in the mid-nineteenth century. Whaling captains, whale ship owners, outfitters, and merchants all benefited from Sag Harbor’s status as one of the three important whaling ports on the East Coast, sending ships to oceans around the world. We are now witnessing a return of that kind of major wealth to the village.

Architecture: Built by Nathan P. Howell, an owner of whale ships, in 1833 and enlarged and remodeled in the Italianate style in 1850. The house is undeniably one of the grandest and most picturesque in Sag Harbor.

Site: The residential part of Main Street has always been a handsome thoroughfare with fine period homes, including some of the largest and most important in the village. But it was hardly legendary, and not to be compared to Gin Lane in Southampton or Lily Pond Lane in East Hampton. That began to change a few years ago, and a recent spate of restoration and a breakthrough in prices has put Main Street in the category of those venerable addresses.

The inside word: Immaculately restored by Nancy Richardson, a New York socialite who knows a thing or two about real estate, this is an historic house of considerable importance. The detailing is perfect and the taste unquestionable. Offered at $9.25 million, and if it sells in that range it will establish a new record for Sag Harbor real estate.

Rustic Refinements

Oh, life is a glorious cycle of song,

A medley of extemporanea;

And love is a thing that can never go wrong;

And I am Marie of Roumania.

Thanks to Dorothy Parker, we often feel like Marie of Roumania. Not relating to love, however, but to real estate. We recently came across this listing, earnestly, purposefully and without irony described by the brokers as a farmhouse. Call us Marie.

Architecture: Barn door details and simple gambrel shapes are suggestive of a rustic outbuilding, but the size and luxuries are more Hamptons than homestead. This property is to farmhouses what Paris Hilton is to farm girls.

Site: Ocean Road in Bridgehampton, 2.5 acres with studio, pool, pool house, tennis court and lots of green lawn.

The inside word: There is still farmland in the neighborhood, but you have to imagine what the whole area was like before housing replaced the fields and farmhouses and barns and outbuildings. It may be a stretch to say that this property honors that tradition, but it certainly evokes the spirit more than sprawling new McMansions do. Offered at $4.995 million.

Level Best

Jon Bon Jovi is going to contract on a house on Lily Pond Lane in East Hampton. And for every famous name, there are dozens of less celebrated but prodigiously rich Wall Street traders and corporate chieftains plunking down millions. Brokers tell us that big-league properties are moving. But they always seem to have more.

Architecture: Clean lined traditional, not as showy and aggressive as newer houses, but certainly gracious.

Site: Southampton estate area, on a delicious, level, hedged 2.8 acres.

The inside word: Conventional keeps coming to mind—but in a most positive way. Handsome house, excellent location, right amenities, nice reasonable size—five bedrooms, five and a half baths, four fireplaces—graced with nice details. It’s a house that seems to have had a happy life. Offered at $6.25 million.

Polished and Proud

We recently attended a seminar on architecture at Guild Hall that included Robert A.M. Stern, dean of architecture at Yale, Peter Wolf, a planner and author of Hot Towns, and Fred Stelle, a modernist architect in Bridgehampton. When the subject of Norman Jaffe came up, all agreed that Jaffe made a major contribution to the refined modernism of the Hamptons in the 1970s and 80s.

Architecture: A sculpted exterior and a harmonious interplay of materials, as precise as a polished diamond.

Site: Superb site on the ocean in Southampton, 2.5 acres with pool and tennis.

The inside word: This taste is not for everyone, not even everyone with $16 million. It takes a sophisticated, swanky and enlightened esthetic, a nose for something cultivated and discerning as opposed to the familiar and the humdrum. Jaffe houses are sought after, and this sublime example of his work is more a collector’s item than simple shelter.

As fabulous as it gets, truly; the beachiest place in the Hamptons: watch out for hurricanes; carriage house crying for restoration; perched on a rocky revetment on Peconic Bay

A house that might have gone to prep school; sliced and diced doughnut of a house; unmistakably establishment and parading its refinement; a ranch house on a real ranch